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Volumn , Issue 3, 2000, Pages 383-388

A new central binaphthalene building block for michellamine syntheses

Author keywords

Biaryls; Binaphthalene building blocks; Cyclizations; Michellamines; Natural products; Protecting groups; Wittig reaction

Indexed keywords

MICHELLAMINE B; NAPHTHALENE DERIVATIVE;

EID: 0034008016     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2000-6340     Document Type: Article
Times cited : (7)

References (41)
  • 6
    • 77957089074 scopus 로고
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    • (a) Bringmann, G.; Pokorny, F. In The Alkaloids, Vol. 46; Cordell, G., Ed.; Academic: New York, 1995; p 127.
    • (1995) The Alkaloids , vol.46 , pp. 127
    • Bringmann, G.1    Pokorny, F.2
  • 28
    • 0343985573 scopus 로고    scopus 로고
    • note
    • A possible alternative access to 6 consisted in its direct preparation by an Ullmann coupling of methyl 4-iodo-3-isopropoxybenzoate, which, however, resulted in less favorable coupling yields (ca. 67%) as compared to the analogous Ullmann reaction of the corresponding 4-iodo-3-methoxybenzoate precursor giving rise to 4 in ca. 80% yield.
  • 32
    • 85088712401 scopus 로고    scopus 로고
    • note
    • 2Bu-t units.
  • 33
    • 0343985571 scopus 로고    scopus 로고
    • note
    • (formula presented) (23) Previous binaphthalene syntheses (see Ref. 16) had used this bromine substituent only for achieving regioselectivity in the cyclization reaction to build up the second naphthalene ring, while in the synthesis described here, the halogen had to be conserved for its additional task as a leaving group in the scheduled later biaryl coupling step (here with the isoquinoline parts).
  • 35
    • 0343113631 scopus 로고    scopus 로고
    • note
    • For analogous reactions on monomeric naphthalenes, see: Refs. 4,8,9b,31.
  • 36
    • 0006078746 scopus 로고    scopus 로고
    • Analytical X-ray Instruments Inc., Madison, Wisconsin 53719, USA
    • Siemens, P4 X-ray Program System, Analytical X-ray Instruments Inc., Madison, Wisconsin 53719, USA, 1996.
    • (1996) P4 X-ray Program System
  • 37
    • 0006072002 scopus 로고
    • Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin 53719, USA
    • Sheldrick, G. M. Program Package SHELXTL-PLUS, Release 4.1, Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin 53719, USA, 1990.
    • (1990) Program Package SHELXTL-PLUS, Release 4.1
    • Sheldrick, G.M.1
  • 38
    • 0342679296 scopus 로고    scopus 로고
    • note
    • A complete listing of the atomic coordinates for 3b can be obtained, on request, from the Cambridge Crystallographic Data Centre, on quoting the depository number CCDC-119273, the names of the authors and the journal citation.
  • 41
    • 0342679294 scopus 로고    scopus 로고
    • Synthesis 2000
    • Watanabe, T.; Uemura, M., Chem. Commun. 1998, 871. Synthesis 2000, No. 3, 389-394
    • (1998) Chem. Commun. , vol.871 , Issue.3 , pp. 389-394
    • Watanabe, T.1    Uemura, M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.